mote.of.soul's first paragraph has been my experience. Keeping the photo a perfect (or near perfect) square seems to be the secret for me. I had the problem a lot in the past and only seemed to solve it when I squared things up a bit.

I remember fiddling with rotation on my phone's and laptop's photo manipulation software and it rarely worked, keeping the photo wide and short (or the opposite). I even tried rotating it 90 degrees where it looked wrong on my side, but hoped it would look OK here (tried to trick it). Again, that rarely helped. Only the squaring up helped with being reliable. Yes, occasionally a rectangular cropped photo worked out, but not sure what the magic secret was, in those rare cases.

As others wrote, this suggested solution may not be all that's to it, but in life if you can make it work, who cares how you manage to do it. I learned that from years of dealing with Microsoft software glitches.